Hydrochloric Acid → (3S)-1-(Cyclohex-1-en-1-ylmethyl)pyrrolidin-3-amine

A mixture of tert-butyl N-[(3S)-1-(cyclohex-1-en-1-ylmethyl)pyrrolidin-3-yl]carbamate obtained in Example 9a (1.3 g, 4.64 mmol) and ethanol (9.2 ml) was stirred under ice-cooling, a 5 N aqueous hydrochloric acid solution (9.28 ml, 46.4 mmol) was added, and the reaction mixture was stirred at room temperature for 14 hours and 30 minutes. The reaction mixture was stirred under ice-cooling, a 5 N aqueous sodium hydroxide solution (9.28 ml, 46.4 mmol) was added, and the solvent was distilled off. Ethanol was added to the residue, the precipitated solid was filtered off, and the solvent in the filtrate was distilled off. Ethanol was further added to the residue, the precipitated solid was filtered off, and the solvent in the filtrate was distilled off to give the title compound (0.8 g, yield 95.6%).

1. temperaturecooling
2. stirringthe reaction mixture was stirred at room temperature for 14 hours and 30 minutes
3. stirringThe reaction mixture was stirred under ice-
4. temperaturecooling
5. distillationthe solvent was distilled off
6. additionEthanol was added to the residue
7. filtrationthe precipitated solid was filtered off
8. distillationthe solvent in the filtrate was distilled off
9. additionEthanol was further added to the residue
10. filtrationthe precipitated solid was filtered off
11. distillationthe solvent in the filtrate was distilled off

ORD record

ord-64b47a5770b34574badc99f813c8ccba

Source dataset

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08476301B2